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CFO THOUGHT LEADER
CFO THOUGHT LEADER
Author: The Future of Finance is Listening
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© Middle Market Media LLC, 2019
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CFO THOUGHT LEADER is a podcast featuring firsthand accounts of finance leaders who are driving change within their organizations.
We share the career journey of our spotlighted CFO guest: What do they struggle with? How do they persevere? What makes them successful CFOs? CFO THOUGHT LEADER is all about inspiring finance professionals to take a leadership leap. We know that by hearing about the successes — (and yes, also the failures) — of others, today’s CFOs can more confidently chart their own leadership paths across the enterprise and take inspired action.
We share the career journey of our spotlighted CFO guest: What do they struggle with? How do they persevere? What makes them successful CFOs? CFO THOUGHT LEADER is all about inspiring finance professionals to take a leadership leap. We know that by hearing about the successes — (and yes, also the failures) — of others, today’s CFOs can more confidently chart their own leadership paths across the enterprise and take inspired action.
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Sam Monti was working in finance at Rockwell Automation when a conversation about charging customers for technical support took an unexpected turn. A salesman suggested collecting a fee for access to the company’s engineers. Monti had another idea: Why not make it a membership, like a country club?The resulting subscription business generated $150 million in revenue in less than three years. For Monti, it was an early lesson in how rethinking a company’s operations could fundamentally change its economics.More than two decades later, that experience has particular relevance at SolarWinds, where Monti is CFO. The IT infrastructure software company has recently moved from public to private ownership under Turn River Capital while completing a transition from license-and-maintenance revenue to subscriptions.Monti views net revenue retention as the critical measure of progress. His framework combines customer retention, annual price increases, and expansion into what he calls the ARR triangle. SolarWinds, he says, is advancing on all three fronts.Meanwhile, the company is investing in agentic AI, including its Avior technology, while working to improve the operational processes that support sales, product development, and future growth.Monti’s career has included large industrial companies, private equity investments, and a difficult turnaround as CEO of Crownpeak. Those experiences have reinforced a conviction about the CFO’s role.“Wars are won by logistics, business is won by operations,” he says.At SolarWinds, that philosophy translates into two priorities: improving operational efficiency and helping the company deploy capital against a clearly defined strategy.
At Greyson Clothiers, opening a new store can mean committing capital long before the first meaningful returns arrive. For CFO Neely Rosen, that gap between investment and payoff has become one of the defining challenges of helping a growing apparel company scale.Greyson's business began in wholesale before expanding into e-commerce and company-owned retail stores. Its Detroit flagship, Rosen notes, has become one of its strongest performers. Now, following a capital raise in late 2024 and a NetSuite implementation, the company is preparing to introduce its own footwear line while expanding its retail presence.The question is how to fund that growth without losing sight of profitability.Rosen's perspective reflects an unconventional career. At Campbell Soup, she moved beyond auditing processes to helping build them during an SAP implementation. At Urban Outfitters, she led a major Oracle systems transformation. Later, as CFO of the Greater Philadelphia YMCA, she developed a leadership philosophy rooted in collaboration and service.Those experiences now inform her approach to technology, talent, and financial decision-making.At Greyson, Rosen works closely with merchandising, production, and supply chain leaders, particularly as tariffs and shifting trade conditions complicate operating decisions. She also sees AI changing what finance teams must deliver: not simply forecasts, but insights that anticipate what comes next.For Rosen, the challenge is deciding when to invest in stores, systems, products, and people—and when those investments should begin producing returns. As Greyson shifts its attention from infrastructure to customers and profitability, capital allocation remains the question occupying her CFO agenda.
For Anaplan CFO Hemant Kapadia, one of the more revealing measures of the company’s transformation isn’t revenue growth alone. It’s the fact that Anaplan has nearly the same number of employees it had when it was taken private in 2022—even as annual recurring revenue has grown from approximately $600 million toward $1.4 billion.The company has also become materially more profitable, generating free cash flow margins in the mid-30s. That financial flexibility has helped fund a $500 million investment commitment spanning infrastructure, platform development, new applications, and artificial intelligence.Yet Kapadia’s ambitions extend beyond Anaplan’s product roadmap.Drawing on an engineering background and 14 years at General Electric, he has long viewed financial performance through an operational lens. Today, that perspective informs Anaplan’s internal AI Readiness program, an initiative he leads to identify opportunities for redesigning processes across the business.Rather than treating AI as another cost-reduction exercise, Kapadia wants employees to reconsider how work gets done—and which activities deserve their attention.“Our approach is not to say we’re gonna implement AI and we’re gonna cut, you know, thirty percent of the organization,” he explains.There’s a similar philosophy behind Anaplan’s own financial operations. By connecting sales forecasts, customer bookings, workforce costs, and cloud expenses, Kapadia says he effectively has a daily financial close, allowing investment decisions to be made during a quarter rather than after it ends.Looking ahead, his challenge is whether Anaplan can double or triple its business while keeping employee growth far below historical norms.For Kapadia, AI’s promise isn’t simply doing the same work faster. It’s changing what the organization can accomplish.
At SuiteWorld 2026, NetSuite’s founder outlines how AI is transforming business software—and what the shift means for CFOs.When Evan Goldberg, founder and executive vice president of Oracle NetSuite, declares that ERP as we know it is over, the statement carries particular weight. Goldberg helped pioneer cloud-based enterprise software in 1998, challenging the conventional wisdom about how businesses should manage their financial and operational systems.Nearly three decades later, he sees artificial intelligence driving an equally consequential transformation.Speaking with CFO Thought Leader at SuiteWorld 2026 in Las Vegas, Goldberg described a future in which ERP systems do more than organize information, automate transactions, and generate reports. Increasingly, they will anticipate problems, recommend solutions, and execute work—with human oversight.Read MoreTo Goldberg, the transformation rests on three developments: AI becoming the primary user interface, ERP becoming tailored to individual businesses, and software gaining the ability to perform more work autonomously.The implications extend well beyond technology.Goldberg believes finance teams will increasingly apply their analytical capabilities across the enterprise, identifying operational issues before they affect financial results. He also sees the traditional month-end close giving way to more continuous financial visibility.Rather than focusing exclusively on achieving a zero-day close, Goldberg argues that CFOs should consider how accurately their systems can reflect the business throughout the reporting period.That shift could fundamentally change how finance contributes to decision-making.“We’re really trying to free up the CFO from firefighting mode to strategic analysis mode,” Goldberg explained.For CFOs, the emerging opportunity is not simply to automate existing responsibilities. It is to redirect financial expertise toward decisions that shape business performance—while increasingly intelligent systems handle more of the underlying work.
When Steve Fox joined Every Man Jack in 2021, the men’s personal care brand had a new private equity owner and an ambitious growth agenda. Carlyle Group saw an opportunity: a widely distributed brand that had never invested heavily in marketing. The challenge was finding the operating leverage to fund that investment.For Fox, the answer increasingly lies in technology.At Every Man Jack, a company known for its outdoor-inspired grooming products, the finance team has remained at five employees even as transaction volume has tripled. Fox credits investments in technology and a growing emphasis on automation.The initiative even has a name: “Nix the Clicks by 26.”The goal is to eliminate manual transactions and replace traditional workflows with functional command centers where employees supervise automated processes, investigate exceptions, and monitor business performance.The transformation gathered momentum after Every Man Jack implemented NetSuite in September 2025. A month later, at SuiteWorld, the company’s IT manager connected the new ERP platform to emerging AI capabilities.Still, Fox recognizes that easier access to technology brings its own complications. With roughly 70 employees suddenly capable of creating software-driven solutions, the company established an AI oversight committee to prevent duplication and keep experimentation aligned with strategy.It’s a distinctly operational approach from a CFO whose career began in public accounting before taking him into retail management and high-growth businesses.And while Fox is enthusiastic about what technology makes possible, his guiding principle remains decidedly human: successful adoption begins with investing in people.











